Salicylohydrazide derivatives, processes and intermediates for their preparation, compositions comprising them, and their use

Info

Publication number: 20020019374
Type: Application
Filed: Jun 14, 2001
Publication Date: Feb 14, 2002
Inventors: Andreas Gypser (Mannheim), Thomas Grote (Wachenheim), Joachim Rheinheimer (Ludwigshafen), Ingo Rose (Mannheim), Peter Schafer (Ottersheim), Oliver Cullmann (Heppenheim), Markus Gewehr (Kastellaun), Wassilios Grammenos (Ludwigshafen), Jordi Tormo i Blasco (Limburgerhof), Bernd Muller (Frankenthal), Hubert Sauter (Mannheim), Eberhard Ammermann (Heppenheim), Siegfried Strathmann (Limburgerhof), Gisela Lorenz (Hambach), Reinhard Stierl (Mutterstadt)
Application Number: 09879902

Abstract

Salicylohydrazide derivatives of the formula I 1

Description

Description

[0001] Salicylohydrazide derivatives, processes and intermediates for their preparation, compositions comprising them, and their use

[0002] The present invention relates to salicylohydrazide derivatives of the formula I 2

[0003] in which the index and the substituents have the following meanings:

[0004] X is halogen, NO2, cyano, C1-C4-alkyl or C1-C4-alkoxy;

[0005] m is 0, 1, 2 or 3, it being possible for the substituents X to differ from each other if n is greater than 1;

[0006] R1 is NO2, NH2 or NH—CO—A;

[0007] A is hydrogen, C1-C4-alkyl, C1-C4-alkoxy, NH2, NHCH3 or N(CH3)2;

[0008] R2 is hydrogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-alkylthio;

[0009] it being possible for the hydrocarbon radicals to be unsubstituted or to be partially or fully halogenated or to have 1 to 3 groups Ra

[0010] Ra is halogen, cyano, nitro, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino,

[0011] di-C1-C6-alkylamino, C2-C6-alkenyl, C3-C6-alkenyloxy, C3-C6-alkynyloxy or C1-C4-alkylenedioxy which can be halogenated,

[0012] R3 is phenyl, naphthyl, C3-C10-cycloalkyl, 5-membered or 6-membered hetaryl or 5-membered or 6-membered heterocyclyl containing one to three N atoms and/or one O or S atom or one or two O and/or S atoms, the ring systems being unsubstituted or substituted by one to three radicals Rb:

[0013] Rb is cyano, nitro, amino, aminocarbonyl, aminothiocarbonyl, halogen, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkyloxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, phenyl, phenoxy, benzyl, benzyloxy, 5- or 6-membered heterocyclyl, 5- or 6-membered hetaryl, 5- or 6-membered hetaryloxy, C(═NOR&agr;)—OR&bgr; or OC(R&agr;)2—C (R&bgr;)═NOR&bgr;,

[0014] the cyclic radicals, in turn, being unsubstituted or substituted by one to three radicals Rc:

[0015] Rc is cyano, nitro, halogen, hydroxyl, amino, aminocarbonyl, aminothiocarbonyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl. C1-C6-alkylthio, C1-C6-alkylamino, di-C-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, phenyl, phenoxy, phenylthio, benzyl, benzyloxy, 5- or 6-membered heterocyclyl, 5- or 6-membered hetaryl, 5- or 6-membered hetaryloxy or C(═NOR&agr;)—OR&bgr;;

[0016] R&agr;, R&bgr; are hydrogen or C1-C6-alkyl.

[0017] Furthermore, the invention relates to processes for the preparation of these compounds, to compositions comprising them, and to their use for controlling harmful fungi.

[0018] WO-A 97/08135, DE-A 197 10 609 and WO-A 99/27783 disclose acylaminosalicylamides for controlling harmful fungi.

[0019] However, their action is unsatisfactory in many cases. Compounds with an improved action are an object of the present invention.

[0020] We have found that this object is achieved by the compounds defined at the outset. Moreover, there have been found processes for their preparation, compositions comprising them, and methods of controlling harmful fungi using the compounds I.

[0021] The compounds of the formula I differ from those known from the prior art by the hydrazide group.

[0022] Compared with the known compounds, the compounds of the formula I exhibit an increased efficacy against harmful fungi.

[0023] For example, compounds of the formula I can be synthesized starting from hydrazides of the formula II by subjecting hydrazides and carbonyl compounds of the formula III to a condensation reaction. The compounds of the formula IA are also used as intermediates for the preparation of further compounds I. 3

[0024] This reaction is usually carried out at temperatures from 20° C. to 100° C., preferably 20° C. to 50° C., in an inert organic solvent in the presence of an acid [cf. Indian J. Chem. B, (1983), Vol. 24, p. 979].

[0025] Suitable solvents are aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methylether, dioxane and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, alcohols such as methanol, ethanol, n-propanol, isopropanol and n-butanol, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide, especially preferably alcohols such as methanol, ethanol, n-propanol, isopropanol and n-butanol. Mixtures of these solvents may also be used.

[0026] Acid and acidic catalysts which are used are inorganic acids such as hydrofluoric acid, (aqueous) hydrochloric acid, tetrabromic acid, sulfuric acid and perchloric acid, Lewis acids such as boron trifluoride, aluminum trichloride, iron(III) chloride, tin(IV) chloride, titanium(IV) chloride and zinc(II) chloride, and organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, citric acid, trifluoroacetic acid, p-toluenesulfonic acid, benzenesulfonic acid and camphorsulfonic acid.

[0027] In general, the acids are employed in catalytic amounts, but they may also be used in equimolar amounts, in an excess or, if appropriate, as solvent.

[0028] In general, the starting materials are reacted with each other in equimolar amounts. It may be advantageous for the yield to employ III in an excess based on II.

[0029] The starting materials II and III required for the preparation of compounds I are commercially available, known from the literature [ZA 70/00662; Labdev, (1973), part A, Vol. 11A(1-2), p. 35] or can be prepared in accordance with the literature cited.

[0030] To prepare compounds I where R1 is NH2 or NH—CO—A, hydrazides of the formula IA are reduced to aminophenol compounds of the formula IB. 4

[0031] The nitro group of IA can be reduced under generally customary conditions by reduction with iron, tin or zinc in the presence of an acid or by enzyme-catalyzed reduction [cf. Houben-Weyl, Vol. IV/1c, 4th Ed., p. 506, Thieme Verlag Stuttgart and New York (1980); ibid. Vol. IV/1d, 4th Ed., p. 473 (1981); Heterocycles (1990), Vol. 31. p. 2201].

[0032] The reaction with hydrogen is preferably carried out by catalytic hydrogenation at −20° C. and +180° C., preferably between −5 and +40° C. The minimum temperature is only determined by the freezing point of the solvent used. Normally, the hydrogenation is carried out at a hydrogen pressure between atmospheric pressure and at an superatmospheric pressure of 30 bar. Normally, the hydrogen is passed in under atmospheric or slight superatmospheric pressure [cf. WO-A 97/08135].

[0033] Catalysts which are employed for the catalytic hydrogenation are commercially available catalysts which comprise, for example, platinum, platinum oxide or palladium on a support, or else Raney nickel or Raney cobalt.

[0034] The use of platinum catalysts or palladium catalysts is preferred. The platinum or palladium content of the catalyst is not critical and can be varied within wide limits. A content of from 0.1 to 15% by weight, preferably from 0.5 to 10% by weight, based on the support material, is expedient. The amount of the platinum or palladium employed is between 0.001 and 10% by weight, preferably between 0.01 and 0.1% by weight, based on the nitro compound. In the preferred embodiment, carbon is used as support material. Other non-amphoteric supports such as graphite, BaSO4 or SiC, are also suitable.

[0035] Suitable diluents are esters such as ethyl acetate, alcohols such as methanol, ethanol, n-propanol, n-, i-, sec- or tert-butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, ethers such as diethylene glycol monomethyl ether, diethylene glycol monomethyl ether, water, aqueous salt solutions such as, for example, ammonium chloride solution, acids, such as, for example, hydrochloric acid or acetic acid; methanol, ethanol and water are especially preferred. Mixtures of these diluents may also be used.

[0036] In general, the acids are employed in catalytic amounts, but they may also be used in equimolar amounts, in an excess or, if appropriate, as solvent.

[0037] To prepare compounds I in which R1 is NH—CO—A, aminophenols of the formula IB are used as intermediates.

[0038] The aminophenols of the formula IB are preferably formylated with formic acid. This gives directly the compounds of the formula I in which R1 is NH—CO—H, which correspond to the formula I.1 5

[0039] This reaction is usually carried out at temperatures of from 20° C. to 100° C., preferably from 20° C. to 80° C., in an inert organic solvent in the presence of an acid.

[0040] Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran. Mixtures of the solvents stated may also be used.

[0041] Acids and acidic catalysts which are used are inorganic acids such as hydrofluoric acid, aqueous hydrochloric acid, hydrobromic acid, sulfuric acid and perchloric acid, Lewis acids such as boron trifluoride, aluminum trichloride, iron(III) chloride, tin(IV) chloride, titanium(IV) chloride and zinc(II) chloride, and organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, citric acid, trifluoroacetic acid, p-toluenesulfonic acid, benzenesulfonic acid and camphorsulfonic acid.

[0042] In general, the acids are employed in catalytic amounts, but they may also be used in equimolar amounts, in an excess or, if appropriate, as solvent.

[0043] In general, the starting materials are reacted with each other in equimolar amounts. It may be advantageous for the yield to employ formic acid in an excess based on V.

[0044] The compounds of the formula IB can be used to obtain the compounds of the formula I in which R1 is NH—CO—A, where A is NH2, NHCH3, N(CH3)2 or OCH3. 6

[0045] The compounds of the formula IB are derivatized to give the compounds of the formulae I.2 to I.6 by means of methods known from the following documents, whose disclosure is herewith incorporated: J. Med. Chem. (1989), Vol. 32, pp. 990-997; J. Org. Chem. (1961), Vol. 26, p. 5238; J. Chem. Res. Synop. (1998), 442; Tetrahedron Lett. (1994). Vol. 35, p. 8761.

[0046] The reaction of IB with alkali metal isocyanates or alkaline earth metal isocyanates, in particular sodium isocyanate, to give urea derivatives I.2 is carried out under the conditions known from J. Med. Chem. (1989), Vol. 32, pp. 990-997.

[0047] The reaction of IB with methyl isocyanate to give urea derivatives I.3 is carried out under the conditions known from J. Org. Chem. (1961), Vol. 26, p. 5238.

[0048] The reaction of IB with dimethylamine and phosgene or a phosgene equivalent such as di- or triphosgene to give urea derivatives I.4 is carried out under the conditions known from J. Chem. Res. Synop. (1998), 442. The use of di- or triphosgene is preferred for practical reasons.

[0049] The reaction of IB with carbon monoxide and methanol to give urea derivatives I.5 is carried out with transition metal catalysis under the conditions known from Tetrahedron Lett. (1994), Vol. 35, p. 8761.

[0050] Compounds of the formula I in which R1 is NH—CO—A where A is C1-C4-alkyl can be obtained from the aminophenol compounds of the formula IB by acylation with alkylcarboxylic acid derivatives of the formula IV in which R4 is C1-C4-alkyl and Z is a nucleophilic leaving group such as alkoxy or halogen. The acylamino derivatives are described by the formula I.6 in which R4 is C1-C4-alkyl. 7

[0051] The acylation of V is carried out under conditions known per se from the literature, it is usually carried out at temperatures of from −20° C. to +80° C., preferably from 0° C. to +60° C., in an inert organic solvent in the presence of a base [cf. Organikum [Organic Chemistry), 15th Ed., p. 508 et seq., VEB Deutscher Verlag der Wissenschaften Berlin (1981)].

[0052] Suitable solvents are water, aliphatic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitrites, ketones, alcohols, and also dimethyl sulfoxide, dimethylformamide and dimethyl acetamide, especially preferably tetrahydrofuran and methylene chloride. Mixtures of the solvents stated may also be used.

[0053] Suitable bases are, in general, inorganic compounds such as alkali metal hydroxides and alkaline earth metal hydroxides, alkali metal oxides and alkaline earth metal oxides, alkali metal hydrides and alkaline earth metal hydrides, alkali metal carbonates and alkaline earth metal carbonates, alkali metal hydrogencarbonates and also alkali metal alkoxides and alkaline earth metal alkoxides, furthermore organic bases, for example tertiary amines such as trimethylamine, triethylamine, tri-isopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidin, lutidin and 4-dimethylaminopyridine, and bicyclic amines. Pyridine and triethylamine are especially preferred. In general, the bases are employed in equimolar amounts, in an excess or, if appropriate, as a solvent.

[0054] In general, the starting materials are reacted with each other in equimolar amounts. It may be advantageous for the yield to employ the reactant(s) in an excess based on IB.

[0055] If individual compounds I are not accessible via the routes described above, they can be prepared by derivatizing other compounds I.

[0056] The reaction mixtures are worked up in the customary manner, for example by mixing with water, separating the phases and, if appropriate, purifying the crude products by chromatography. Some of the intermediates and end products are obtained in the form of colorless or pale brown, viscous oils, which are purified or freed from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, they may also be purified by recrystallization or digestion.

[0057] In the definitions of the symbols in the above formulae, collective terms were used which generally represent the following substituents:

[0058] halogen: fluorine, chlorine, bromine and iodine;

[0059] alkyl: saturated, straight-chain or branched hydrocarbon radicals having 1 to 4, 6, 8 or 10 carbon atoms, for example C1-C6-alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;

[0060] halogenalkyl: straight-chain or branched alkyl groups having 1 to 10 carbon atoms (as mentioned above), it being possible for some or all of the hydrogen atoms in these groups to be replaced by halogen atoms as mentioned above, for example C1-C2-haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;

[0061] alkoxy: straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as mentioned above) which are bonded to the skeleton via an oxygen atom (—O—);

[0062] alkenyl: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4 or 6 carbon atoms and one double bond in any position, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-i-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;

[0063] alkynyl: straight-chain or branched hydrocarbon groups having 2 to 4 or 6 carbon atoms and one triple bond in any position, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;

[0064] cycloalkyl: monocyclic saturated hydrocarbon groups saving 3 to 6 carbon ring members such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

[0065] 5- or 6-membered heterocyclyl contains, in addition to carbon ring members, one to three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygen and/or sulfur atoms, e.g. 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl and 1,2,4-hexahydrotriazin-3-yl;

[0066] 5-membered heteroaryl contains one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom: 5-membered cyclic heteroaryl groups which, besides carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members, e.g. 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl and 1,3,4-triazol-2-yl;

[0067] 6-membered heteroaryl contains one to three or one to four nitrogen atoms: 6-membered cyclic heteroaryl groups which, besides carbon atoms, may contain one to three or one to four nitrogen atoms as ring members, e.g. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl;

[0068] alkylene: divalent unbranched chains made up by 1 to 4 CH2 groups, e.g. CH2, CH2CH2, CH2CH2CH2 and CH2CH2CH2CH2;

[0069] alkylenedioxy: divalent unbranched chains made up of 1 to 3 CH2 groups, both valencies being bound to the skeleton via an oxygen atom, e.g. OCH2O, OCH2CH2O and OCH2CH2CH2O.

[0070] With regard of the intended use of the salicylohydrazide derivatives of the formula I, the following meanings of the substituents are especially preferred, in each case alone or in combination:

[0071] Especially preferred are compounds of the formula IA. 8

[0072] Especially preferred are compounds of the formula I where R1 is NH—CO—A; these compounds are described with the formula IC: 9

[0073] Also especially preferred are compounds I.1.

[0074] Equally, other preferred compounds are those of the formula I.6 where R4 is methyl; these compounds are described by the formula I.6a: 10

[0075] Besides, especially preferred compounds I are those where the index m is zero; these compounds are described by the formula ID: 11

[0076] In addition, especially preferred compounds I are those where (X)m is in the para-position relative to the phenol-OH group and is halogen, NO2, CN and C1-C4-alkoxy, in particular 4-chloro, 4-bromo and 4-NO2.

[0077] Equally especially preferred are compounds I where R2 is hydrogen, methyl, ethyl, n-propyl, isopropyl and cyano, in particular hydrogen and methyl.

[0078] Other particularly preferred compounds I are those where R3 is cyclohexyl and phenyl, each of which is optionally substituted by one to three radicals Rb, in particular phenyl. In the case of compounds in which R3 is cyclohexyl, the substituent Rb can be in the E- or Z-position relative to the C—R3 bond.

[0079] In addition, especially preferred compounds I are those where R3 is pyrazolyl, pyrimidinyl, pyridinyl, pyrazinyl and thiophenyl, each of which is optionally substituted by one to three radicals Rb.

[0080] The especially preferred use forms of the intermediates with regard to the variables correspond to those of the radicals (X)m, R1, A, R2 and R3 of the formula I.

[0081] Especially preferred with regard to their use are the compounds I which are compiled in the following tables. In the tables, the groups mentioned for a substituent additionally represent an especially preferred embodiment of the substituent in question in their own right, independently of the combination in which they are mentioned.

[0082] Table 1

[0083] Compounds of the formula IA where m is zero, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A 12

[0084] Table 2

[0085] Compounds of the formula IA where m is zero, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0086] Table 3

[0087] Compounds of the formula IA where m is zero, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0088] Table 4

[0089] Compounds of the formula IA where m is zero, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0090] Table 5

[0091] Compounds of the formula IA where m is zero, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0092] Table 6

[0093] Compounds of the formula IA where m is zero, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0094] Table 7

[0095] Compounds of the formula IA where (X)m is 3-chloro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0096] Table 8

[0097] Compounds of the formula IA where (X)m is 3-chloro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0098] Table 9

[0099] Compounds of the formula IA where (X)m is 3-chloro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0100] Table 10

[0101] Compounds of the formula IA where (X)m is 3-chloro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0102] Table 11

[0103] Compounds of the formula IA where (X)m is 3-chloro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0104] Table 12

[0105] Compounds of the formula IA where (X)m is 3-chloro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0106] Table 13

[0107] Compounds of the formula IA where (X)m is 4-chloro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0108] Table 14

[0109] Compounds of the formula IA where (X)m is 4-chloro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0110] Table 15

[0111] Compounds of the formula IA where (X)m is 4-chloro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0112] Table 16

[0113] Compounds of the formula IA where (X)m is 4-chloro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0114] Table 17

[0115] Compounds of the formula IA where (X)m is 4-chloro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0116] Table 18

[0117] Compounds of the formula IA where (X)m is 4-chloro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0118] Table 19

[0119] Compounds of the formula IA where (X)m is 5-chloro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0120] Table 20

[0121] Compounds of the formula IA where (X)m is 5-chloro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0122] Table 21

[0123] Compounds of the formula IA where (X)m is 5-chloro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0124] Table 22

[0125] Compounds of the formula IA where (X)m is 5-chloro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0126] Table 23

[0127] Compounds of the formula IA where (X)m is 5-chloro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0128] Table 24

[0129] Compounds of the formula IA where (X)m is 5-chloro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0130] Table 25

[0131] Compounds of the formula IA where (X)m is 3-bromo, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0132] Table 26

[0133] Compounds of the formula IA where (X)m is 3-bromo, R2 is methyl and the radical R3 or each compound corresponds to one line of Table A

[0134] Table 27

[0135] Compounds of the formula IA where (X)m is 3-bromo, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0136] Table 28

[0137] Compounds of the formula IA where (X)m is 3-bromo, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0138] Table 29

[0139] Compounds of the formula IA where (X)m is 3-bromo, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0140] Table 30

[0141] Compounds of the formula IA where (X)m is 3-bromo, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0142] Table 31

[0143] compounds of the formula IA where (X)m is 4-bromo, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0144] Table 32

[0145] Compounds of the formula IA where (X)m is 4-bromo, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0146] Table 33

[0147] Compounds of the formula IA where (X)m is 4-bromo, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0148] Table 34

[0149] Compounds of the formula IA where (X)m is 4-bromo, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0150] Table 35

[0151] Compounds of the formula IA where (X)m is 4-bromo, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0152] Table 36

[0153] Compounds of the formula IA where (X)m is 4-bromo, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0154] Table 37

[0155] Compounds of the formula IA where (X)m is 5-bromo, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0156] Table 38

[0157] Compounds of the formula IA where (X)m is 5-bromo, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0158] Table 39

[0159] Compounds of the formula IA where (X)m is 5-bromo, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0160] Table 40

[0161] Compounds of the formula IA where (X)m is 5-bromo, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0162] Table 41

[0163] Compounds of the formula IA where (X)m is 5-bromo, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0164] Table 42

[0165] Compounds of the formula IA where (X)m is 5-bromo, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0166] Table 43

[0167] Compounds of the formula IA where (X)m is 3-nitro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0168] Table 44

[0169] Compounds of the formula IA where (X)m is 3-nitro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0170] Table 45

[0171] Compounds of the formula IA there (X)m is 3-nitro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0172] Table 46

[0173] Compounds of the formula IA where (X)m is 3-nitro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0174] Table 47

[0175] Compounds of the formula IA where (X)m is 3-nitro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0176] Table 48

[0177] Compounds of the formula IA where (X)m is 3-nitro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0178] Table 49

[0179] Compounds of the formula IA where (X)m is 4-nitro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0180] Table 50

[0181] Compounds of the formula IA where (X)m is 4-nitro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0182] Table 51

[0183] Compounds of the formula IA where (X)m is 4-nitro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0184] Table 52

[0185] Compounds of the formula IA where (X)m is 4-nitro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0186] Table 53

[0187] Compounds of the formula IA where (X)m is 4-nitro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0188] Table 54

[0189] Compounds of the formula IA where (X)m is 4-nitro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0190] Table 55

[0191] Compounds of the formula IA where (X)m is 5-nitro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0192] Table 56

[0193] Compounds of the formula IA where (X)m is 5-nitro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0194] Table 57

[0195] Compounds of the formula IA where (X)m is 5-nitro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0196] Table 58

[0197] Compounds of the formula IA where (X)m is 5-nitro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0198] Table 59

[0199] Compounds of the formula IA where (X)m is 5-nitro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0200] Table 60

[0201] Compounds of the formula IA where (X)m is 5-nitro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0202] Table 61

[0203] Compounds of the formula IB where m is zero, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A 13

[0204] Table 62

[0205] Compounds of the formula IB where m is zero, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0206] Table 63

[0207] Compounds of the formula IB where m is zero, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0208] Table 64

[0209] Compounds of the formula IB where m is zero, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0210] Table 65

[0211] Compounds of the formula IB where m is zero, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0212] Table 66

[0213] Compounds of the formula IB where m is zero, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0214] Table 67

[0215] Compounds of the formula IB where (X)m is 3-chloro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0216] Table 68

[0217] Compounds of the formula IB where (X)m is 3-chloro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0218] Table 69

[0219] Compounds of the formula IB where (X)m is 3-chloro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0220] Table 70

[0221] Compounds of the formula IB where (X)m is 3-chloro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0222] Table 71

[0223] Compounds of the formula IB where (X)m is 3-chloro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0224] Table 72

[0225] Compounds of the formula IB where (X)m is 3-chloro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0226] Table 73

[0227] Compounds of the formula IB where (X)m is 4-chloro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0228] Table 74

[0229] Compounds of the formula IB where (X)m is 4-chloro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0230] Table 75

[0231] Compounds of the formula IB where (X)m is 4-chloro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0232] Table 76

[0233] Compounds of the formula IB where (X)m is 4-chloro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0234] Table 77

[0235] Compounds of the formula IB where (X)m is 4-chloro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0236] Table 78

[0237] Compounds of the formula IB where (X)m is 4-chloro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0238] Table 79

[0239] Compounds of the formula IB where (X)m is 5-chloro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0240] Table 80

[0241] Compounds of the formula IB where (X)m is 5-chloro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0242] Table 81

[0243] Compounds of the formula IB where (X)m is 5-chloro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0244] Table 82

[0245] Compounds of the formula IB where (X)m is 5-chloro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0246] Table 83

[0247] Compounds of the formula IB where (X)m is 5-chloro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0248] Table 84

[0249] Compounds of the formula IB where (X)m is 5-chloro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0250] Table 85

[0251] Compounds of the formula IB where (X)m is 3-bromo, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0252] Table 86

[0253] Compounds of the formula IB where (X)m is 3-bromo, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0254] Table 87

[0255] Compounds of the formula IB where (X)m is 3-bromo, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0256] Table 88

[0257] Compounds of the formula IB where (X)m is 3-bromo, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0258] Table 89

[0259] Compounds of the formula IB where (X)m is 3-bromo, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0260] Table 90

[0261] Compounds of the formula IB where (X)m is 3-bromo, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0262] Table 91

[0263] Compounds of the formula IB where (X)m is 4-bromo, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0264] Table 92

[0265] Compounds of the formula IB where (X)m is 4-bromo, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0266] Table 93

[0267] Compounds of the formula IB where (X)m is 4-bromo, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0268] Table 94

[0269] Compounds of the formula IB where (X)m is 4-bromo, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0270] Table 95

[0271] Compounds of the formula IB where (X)m is 4-bromo, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0272] Table 96

[0273] Compounds of the formula IB where (X)m is 4-bromo, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0274] Table 97

[0275] Compounds of the formula IB where (X)m is 5-bromo, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0276] Table 98

[0277] Compounds of the formula IB where (X)m is 5-bromo, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0278] Table 99

[0279] Compounds of the formula IB where (X)m is 5-bromo, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0280] Table 100

[0281] Compounds of the formula IB where (X)m is 5-bromo, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0282] Table 101

[0283] Compounds of the formula IB where (X)m is 5-bromo, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0284] Table 102

[0285] Compounds of the formula IB where (X)m is 5-bromo. R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0286] Table 103

[0287] Compounds of the formula IB where (X)m is 3-nitro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0288] Table 104

[0289] Compounds of the formula IB where (X)m is 3-nitro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0290] Table 105

[0291] Compounds of the formula IB where (X)m is 3-nitro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0292] Table 106

[0293] Compounds of the formula IB where (X)m is 3-nitro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0294] Table 107

[0295] Compounds of the formula IB where (X)m is 3-nitro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0296] Table 108

[0297] Compounds of the formula IB where (X)m is 3-nitro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0298] Table 109

[0299] Compounds of the formula IB where (X)m is 4-nitro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0300] Table 110

[0301] Compounds of the formula IB where (X)m is 4-nitro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0302] Table 111

[0303] Compounds of the formula IB where (X)m is 4-nitro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table

[0304] Table 112

[0305] Compounds of the formula IB where (X)m is 4-nitro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0306] Table 113

[0307] Compounds of the formula IB where (X)m is 4-nitro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0308] Table 114

[0309] Compounds of the formula IB where (X)m is 4-nitro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0310] Table 115

[0311] Compounds of the formula IB where (X)m is 5-nitro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0312] Table 116

[0313] Compounds of the formula IB where (X)m is 5-nitro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0314] Table 117

[0315] Compounds of the formula IB where (X)m is 5-nitro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0316] Table 118

[0317] Compounds of the formula IB where (X)m is 5-nitro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0318] Table 119

[0319] Compounds of the formula IB where (X)m is 5-nitro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0320] Table 120

[0321] Compounds of the formula IB where (X)m is 5-nitro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0322] Table 121

[0323] Compounds of the formula I.1 where m is zero, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A 14

[0324] Table 122

[0325] Compounds of the formula I.1 where m is zero, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0326] Table 123

[0327] Compounds of the formula I.1 where m is zero, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0328] Table 124

[0329] Compounds of the formula I.1 where m is zero, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0330] Table 125

[0331] Compounds of the formula I.1 where m is zero, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0332] Table 126

[0333] Compounds of the formula I.1 where m is zero, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0334] Table 127

[0335] Compounds of the formula I.1 where (X)m is 3-chloro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0336] Table 128

[0337] Compounds of the formula I.1 where (X)m is 3-chloro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0338] Table 129

[0339] Compounds of the formula I.1 where (X)m is 3-chloro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0340] Table 130

[0341] Compounds of the formula I.1 where (X)m is 3-chloro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0342] Table 131

[0343] Compounds of the formula I.1 where (X)m is 3-chloro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0344] Table 132

[0345] Compounds of the formula I.1 where (X)m is 3-chloro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0346] Table 133

[0347] Compounds of the formula I.1 where (X)m is 4-chloro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0348] Table 134

[0349] Compounds of the formula I.1 where (X)m is 4-chloro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0350] Table 135

[0351] Compounds of the formula I.1 where (X)m is 4-chloro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0352] Table 136

[0353] Compounds of the formula I.1 where (X)m is 4-chloro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0354] Table 137

[0355] Compounds of the formula I.1 where (X)m is 4-chloro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0356] Table 138

[0357] Compounds of the formula I.1 where (X)m is 4-chloro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0358] Table 139

[0359] Compounds of the formula I.1 where (X)m is 5-chloro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0360] Table 140

[0361] Compounds of the formula I.1 where (X)m is 5-chloro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0362] Table 141

[0363] Compounds of the formula I.1 where (X)m is 5-chloro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0364] Table 142

[0365] Compounds of the formula I.1 where (X)m is 5-chloro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0366] Table 143

[0367] Compounds of the formula I.1 where (X)m is 5-chloro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0368] Table 144

[0369] Compounds of the formula I.1 where (X)m is 5-chloro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0370] Table 145

[0371] Compounds of the formula I.1 where (X)m is 3-bromo, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0372] Table 146

[0373] Compounds of the formula I.1 where (X)m is 3-bromo, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0374] Table 147

[0375] Compounds of the formula I.1 where (X)m is 3-bromo, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0376] Table 148

[0377] Compounds of the formula I.1 where (X)m is 3-bromo, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0378] Table 149

[0379] Compounds of the formula I.1 where (X)m is 3-bromo, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0380] Table 150

[0381] Compounds of the formula I.1 where (X)m is 3-bromo R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0382] Table 151

[0383] Compounds of the formula I.1 where (X)m is 4-bromo, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0384] Table 152

[0385] Compounds of the formula I.1 where (X)m is 4-bromo, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0386] Table 153

[0387] Compounds of the formula I.1 where (X)m is 4-bromo, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0388] Table 154

[0389] Compounds of the formula I.1 where (X)m is 4-bromo, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0390] Table 155

[0391] Compounds of the formula I.1 where (X)m is 4-bromo, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0392] Table 156

[0393] Compounds of the formula I.1 where (X)m is 4-bromo, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0394] Table 157

[0395] Compounds of the formula I.1 where (X)m is 5-bromo, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0396] Table 158

[0397] Compounds of the formula I.1 where (X)m is 5-bromo, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0398] Table 159

[0399] Compounds of the formula I.1 where (X)m is 5-bromo, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0400] Table 160

[0401] Compounds of the formula I.1 where (X)m is 5-bromo, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0402] Table 161

[0403] Compounds of the formula I.1 where (X)m is 5-bromo, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0404] Table 162

[0405] Compounds of the formula I.1 where (X)m is 5-bromo, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0406] Table 163

[0407] Compounds of the formula I.1 where (X)m is 3-nitro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0408] Table 164

[0409] Compounds of the formula I.1 where (X)m is 3-nitro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0410] Table 165

[0411] Compounds of the formula I.1 where (X)m is 3-nitro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0412] Table 166

[0413] Compounds of the formula I.1 where (X)m is 3-nitro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0414] Table 167

[0415] Compounds of the formula I.1 where (X)m is 3-nitro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0416] Table 168

[0417] Compounds of the formula I.1 where (X)m is 3-nitro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0418] Table 169

[0419] Compounds of the formula I.1 where (X)m is 4-nitro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0420] Table 170

[0421] Compounds of the formula I.1 where (X)m is 4-nitro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0422] Table 171

[0423] Compounds of the formula I.1 where (X)m is 4-nitro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0424] Table 172

[0425] Compounds of the formula I.1 where (X)m is 4-nitro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0426] Table 173

[0427] Compounds of the formula I.1 where (X)m is 4-nitro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0428] Table 174

[0429] Compounds of the formula I.1 where (X)m is 4-nitro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0430] Table 175

[0431] Compounds of the formula I.1 where (X)m is 5-nitro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0432] Table 176

[0433] Compounds of the formula I.1 where (X)m is 5-nitro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0434] Table 177

[0435] Compounds of the formula I.1 where (X)m is 5-nitro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0436] Table 178

[0437] Compounds of the formula I.1 where (X)m is 5-nitro, R2 is n-propyl and the radical R2 for each compound corresponds to one line of Table A

[0438] Table 179

[0439] Compounds of the formula I.1 where (X)m is 5-nitro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0440] Table 180

[0441] Compounds of the formula I.1 where (X)m is 5-nitro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0442] Table 181

[0443] Compounds of the formula I.2 where m is zero, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A 15

[0444] Table 182

[0445] Compounds of the formula I.2 where m is zero, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0446] Table 183

[0447] Compounds of the formula I.2 where m is zero, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0448] Table 184

[0449] Compounds of the formula I.2 where m is zero, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0450] Table 185

[0451] Compounds of the formula I.2 where m is zero, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0452] Table 186

[0453] Compounds of the formula I.2 where m is zero, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0454] Table 187

[0455] Compounds of the formula I.2 where (X)m is 3-chloro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0456] Table 188

[0457] Compounds of the formula I.2 where (X)m is 3-chloro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0458] Table 189

[0459] Compounds of the formula I.2 where (X)m is 3-chloro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0460] Table 190

[0461] Compounds of the formula I.2 where (X)m is 3-chloro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0462] Table 191

[0463] Compounds of the formula I.2 where (X)m is 3-chloro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0464] Table 192

[0465] Compounds of the formula I.2 where (X)m is 3-chloro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0466] Table 193

[0467] Compounds of the formula I.2 where (X)m is 4-chloro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0468] Table 194

[0469] Compounds of the formula I.2 where (X)m is 4-chloro, R2 is methyl and the radical R2 for each compound corresponds to one line of Table A

[0470] Table 195

[0471] Compounds of the formula I.2 where (X)m is 4-chloro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0472] Table 196

[0473] Compounds of the formula I.2 where (X)m is 4-chloro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0474] Table 197

[0475] Compounds of the formula I.2 where (X)m is 4-chloro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0476] Table 198

[0477] Compounds of the formula I.2 where (X)m is 4-chloro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0478] Table 199

[0479] Compounds of the formula I.2 where (X)m is 5-chloro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0480] Table 200

[0481] Compounds of the formula I.2 where (X)m is 5-chloro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0482] Table 201

[0483] Compounds of the formula I.2 where (X)m is 5-chloro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0484] Table 202

[0485] Compounds of the formula I.2 where (X)m is 5-chloro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0486] Table 203

[0487] Compounds of the formula I.2 where (X)m is 5-chloro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0488] Table 204

[0489] Compounds of the formula I.2 where (X)m is 5-chloro, R2 is cyano and the radical R2 for each compound corresponds to one line of Table A

[0490] Table 205

[0491] Compounds of the formula I.2 where (X)m is 3-bromo, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0492] Table 206

[0493] Compounds of the formula I.2 where (X)m is 3-bromo, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0494] Table 207

[0495] Compounds of the formula I.2 where (X)m is 3-bromo, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0496] Table 208

[0497] Compounds of the formula I.2 where (X)m is 3-bromo, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0498] Table 209

[0499] Compounds of the formula I.2 where (X)m is 3-bromo, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0500] Table 210

[0501] Compounds of the formula I.2 where (X)m is 3-bromo, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0502] Table 211

[0503] Compounds of the formula I.2 where (X)m is 4-bromo, 2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0504] Table 212

[0505] Compounds of the formula I.2 where (X)m is 4-bromo, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0506] Table 213

[0507] Compounds of the formula I.2 where (X)m is 4-bromo, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0508] Table 214

[0509] Compounds of the formula I.2 where (X)m is 4-bromo, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0510] Table 215

[0511] Compounds of the formula I.2 where (X)m is 4-bromo, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0512] Table 216

[0513] Compounds of the formula I.2 where (X)m is 4-bromo, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0514] Table 217

[0515] Compounds of the formula I.2 where (X)m is 5-bromo, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0516] Table 218

[0517] Compounds of the formula I.2 where (X)m is 5-bromo, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0518] Table 219

[0519] Compounds of the formula I.2 where (X)m is 5-bromo, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0520] Table 220

[0521] Compounds of the formula I.2 where (X)m is 5-bromo, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0522] Table 221

[0523] Compounds of the formula I.2 where (X)m is 5-bromo, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0524] Table 222

[0525] Compounds of the formula I.2 where (X)hd m is 5-bromo, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0526] Table 223

[0527] Compounds of the formula I.2 where (X)m is 3-nitro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0528] Table 224

[0529] Compounds of the formula I.2 where (X)m is 3-nitro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0530] Table 225

[0531] Compounds of the formula I.2 where (X)m is 3-nitro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0532] Table 226

[0533] Compounds of the formula I.2 where (X)m is 3-nitro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0534] Table 227

[0535] Compounds of the formula I.2 where (X)m is 3-nitro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0536] Table 228

[0537] Compounds of the formula I.2 where (X)m is 3-nitro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0538] Table 229

[0539] Compounds of the formula I.2 where (X)m is 4-nitro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0540] Table 230

[0541] Compounds of the formula I.2 where (X)m is 4-nitro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0542] Table 231

[0543] Compounds of the formula I.2 where (X)m is 4-nitro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0544] Table 232

[0545] Compounds of the formula I.2 where (X)m is 4-nitro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0546] Table 233

[0547] Compounds of the formula I.2 where (X)m is 4-nitro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0548] Table 234

[0549] Compounds of the formula I.2 where (X)m is 4-nitro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0550] Table 235

[0551] Compounds of the formula I.2 where (X)m is 5-nitro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0552] Table 236

[0553] Compounds of the formula I.2 where (X)m is 5-nitro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0554] Table 237

[0555] Compounds of the formula I.2 where (X)m is 5-nitro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0556] Table 238

[0557] Compounds of the formula I.2 where (X)m is 5-nitro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0558] Table 239

[0559] Compounds of the formula I.2 where (X)m is 5-nitro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0560] Table 240

[0561] Compounds of the formula I.2 where (X)m is 5-nitro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0562] Table 241

[0563] Compounds of the formula I.3 where m is zero, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A 16

[0564] Table 242

[0565] Compounds of the formula I.3 where m is zero, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0566] Table 243

[0567] Compounds of the formula I.3 where m is zero, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0568] Table 244

[0569] Compounds of the formula I.3 where m is zero, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0570] Table 245

[0571] Compounds of the formula I.3 where m is zero, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0572] Table 246

[0573] Compounds of the formula I.3 where m is zero, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0574] Table 247

[0575] Compounds of the formula I.3 where (X)m is 3-chloro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0576] Table 248

[0577] Compounds of the formula I.3 where (X)m is 3-chloro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0578] Table 249

[0579] Compounds of the formula I.3 where (X)m is 3-chloro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0580] Table 250

[0581] Compounds of the formula I.3 where (X)m is 3-chloro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0582] Table 251

[0583] Compounds of the formula I.3 there (X)m is 3-chloro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0584] Table 252

[0585] Compounds of the formula I.3 where (X)m is 3-chloro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0586] Table 253

[0587] Compounds of the formula I.3 where (X)m is 4-chloro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0588] Table 254

[0589] Compounds of the formula I.3 where (X)m is 4-chloro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0590] Table 255

[0591] Compounds of the formula I.3 where (X)m is 4-chloro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0592] Table 256

[0593] Compounds of the formula I.3 where (X)m is 4-chloro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0594] Table 257

[0595] Compounds of the formula I.3 where (X)m is 4-chloro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0596] Table 258

[0597] Compounds of the formula I.3 where (X)m is 4-chloro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0598] Table 259

[0599] Compounds of the formula I.3 where (X)m is 5-chloro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0600] Table 260

[0601] Compounds of the formula I.3 where (X)m is 5-chloro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0602] Table 261

[0603] Compounds of the formula I.3 where (X)m is 5-chloro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0604] Table 262

[0605] Compounds of the formula I.3 where (X)m is 5-chloro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0606] Table 263

[0607] Compounds of the formula I.3 where (X)m is 5-chloro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0608] Table 264

[0609] Compounds of the formula I.3 where (X)m is 5-chloro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0610] Table 265

[0611] Compounds of the formula I.3 where (X)m is 3-bromo, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0612] Table 266

[0613] Compounds of the formula I.3 where (X)m is 3-bromo, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0614] Table 267

[0615] Compounds of the formula I.3 where (X)m is 3-bromo, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0616] Table 268

[0617] Compounds of the formula I.3 where (X)m is 3-bromo, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0618] Table 269

[0619] Compounds of the formula I.3 where (X)m is 3-bromo, R2 as isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0620] Table 270

[0621] Compounds of the formula I.3 where (X)m is 3-bromo, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0622] Table 271

[0623] Compounds of the formula I.3 where (X)m is 4-bromo, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0624] Table 272

[0625] Compounds of the formula I.3 where (X)m is 4-bromo, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0626] Table 273

[0627] Compounds of the formula I.3 where (X)m is 4-bromo, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0628] Table 274

[0629] Compounds of the formula I.3 where (X)m is 4-bromo, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0630] Table 275

[0631] Compounds of the formula I.3 where (X)m is 4-bromo, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0632] Table 276

[0633] Compounds of the formula I.3 where (X)m is 4-bromo, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0634] Table 277

[0635] Compounds of the formula I.3 where (X)m is 5-bromo, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0636] Table 278

[0637] Compounds of the formula I.3 where (X)m is 5-bromo, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0638] Table 279

[0639] Compounds of the formula I.3 where (X)m is 5-bromo, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0640] Table 280

[0641] Compounds of the formula I.3 where (X)m is 5-bromo, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0642] Table 281

[0643] Compounds of the formula I.3 where (X)m is 5-bromo, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0644] Table 282

[0645] Compounds of the formula I.3 where (X)m is 5-bromo, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0646] Table 283

[0647] Compounds of the formula I.3 where (X)m is 3-nitro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0648] Table 284

[0649] Compounds of the formula I.3 where (X)m is 3-nitro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0650] Table 285

[0651] Compounds of the formula I.3 where (X)m is 3-nitro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0652] Table 286

[0653] Compounds of the formula I.3 where (X)m is 3-nitro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0654] Table 287

[0655] Compounds of the formula I.3 where (X)m is 3-nitro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0656] Table 288

[0657] Compounds of the formula I.3 where (X)m is 3-nitro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0658] Table 289

[0659] Compounds of the formula I.3 where (X)m is 4-nitro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0660] Table 290

[0661] Compounds of the formula I.3 where (X)m is 4-nitro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0662] Table 291

[0663] Compounds of the formula I.3 where (X)m is 4-nitro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0664] Table 292

[0665] Compounds of the formula I.3 where (X)m is 4-nitro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0666] Table 293

[0667] Compounds of the formula I.3 where (X)m is 4-nitro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0668] Table 294

[0669] Compounds of the formula I.3 where (X)m is 4-nitro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0670] Table 295

[0671] Compounds of the formula I.3 where (X)m is 5-nitro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0672] Table 296

[0673] Compounds of the formula I.3 where (X)m is 5-nitro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0674] Table 297

[0675] Compounds of the formula I.3 where (X)m is 5-nitro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0676] Table 298

[0677] Compounds of the formula I.3 where (X)m is 5-nitro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0678] Table 299

[0679] Compounds of the formula I.3 where (X)m is 5-nitro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0680] Table 300

[0681] Compounds of the formula I.3 where (X)m is 5-nitro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0682] Table 301

[0683] Compounds of the formula I.5 where m is zero, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A 17

[0684] Table 302

[0685] Compounds of the formula I.5 where m is zero, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0686] Table 303

[0687] Compounds of the formula I.5 where m is zero, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0688] Table 304

[0689] Compounds of the formula I.5 where m is zero, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0690] Table 305

[0691] Compounds of the formula I.5 where m is zero, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0692] Table 306

[0693] Compounds of the formula I.5 where m is zero, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0694] Table 307

[0695] Compounds of the formula I.5 where (X)m is 3-chloro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0696] Table 308

[0697] Compounds of the formula I.5 where (X)m is 3-chloro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0698] Table 309

[0699] Compounds of the formula I.5 where (X)m is 3-chloro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0700] Table 310

[0701] Compounds of the formula I.5 where (X)m is 3-chloro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0702] Table 311

[0703] Compounds of the formula I.5 where (X)m is 3-chloro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0704] Table 312

[0705] Compounds of the formula I.5 where (X)m is 3-chloro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0706] Table 313

[0707] Compounds of the formula I.5 where (X)m is 4-chloro, R2 is hydrogen and the radical R2 for each compound corresponds to one line of Table A

[0708] Table 314

[0709] Compounds of the formula I.5 where (X)m is 4-chloro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0710] Table 315

[0711] Compounds of the formula I.5 where (X)m is 4-chloro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0712] Table 316

[0713] Compounds of the formula I.5 where (X)m is 4-chloro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0714] Table 317

[0715] Compounds of the formula I.5 where (X)m is 4-chloro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0716] Table 318

[0717] Compounds of the formula I.5 where (X)m is 4-chloro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0718] Table 319

[0719] Compounds of the formula I.5 where (X)m is 5-chloro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0720] Table 320

[0721] Compounds of the formula I.5 where (X)m is 5-chloro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0722] Table 321

[0723] Compounds of the formula I.5 where (X)m is 5-chloro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0724] Table 322

[0725] Compounds of the formula I.5 where (X)m is 5-chloro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0726] Table 323

[0727] Compounds of the formula I.5 where (X)m is 5-chloro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0728] Table 324

[0729] Compounds of the formula I.5 where (X)m is 5-chloro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0730] Table 325

[0731] Compounds of the formula I.5 where (X)m is 3-bromo, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0732] Table 326

[0733] Compounds of the formula I.5 where (X)m is 3-bromo, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0734] Table 327

[0735] Compounds of the formula I.5 where (X)m is 3-bromo, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0736] Table 328

[0737] Compounds of the formula I.5 where (X)m is 3-bromo, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0738] Table 329

[0739] Compounds of the formula I.5 where (X)m is 3-bromo, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0740] Table 330

[0741] Compounds of the formula I.5 where (X)m is 3-bromo, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0742] Table 331

[0743] Compounds of the formula I.5 where (X)m is 4-bromo, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0744] Table 332

[0745] Compounds of the formula I.5 where (X)m is 4-bromo, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0746] Table 333

[0747] Compounds of the formula I.5 where (X)m is 4-bromo, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0748] Table 334

[0749] Compounds of the formula I.5 where (X)m is 4-bromo, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0750] Table 335

[0751] Compounds of the formula I.5 where (X)m is 4-bromo, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0752] Table 336

[0753] Compounds of the formula I.5 where (X)m is 4-bromo, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0754] Table 337

[0755] Compounds of the formula I.5 where (X)m is 5-bromo, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0756] Table 338

[0757] Compounds of the formula I.5 where (X)m is 5-bromo, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0758] Table 339

[0759] Compounds of the formula I.5 where (X)m is 5-bromo, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0760] Table 340

[0761] Compounds of the formula I.5 where (X)m is 5-bromo, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0762] Table 341

[0763] Compounds of the formula I.5 where (X)m is 5-bromo, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0764] Table 342

[0765] Compounds of the formula I.5 where (X)m is 5-bromo, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0766] Table 343

[0767] Compounds of the formula I.5 where (X)m is 3-nitro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0768] Table 344

[0769] Compounds of the formula I.5 where (X)m is 3-nitro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0770] Table 345

[0771] Compounds of the formula I.5 where (X)m is 3-nitro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0772] Table 346

[0773] Compounds of the formula I.5 where (X)m is 3-nitro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0774] Table 347

[0775] Compounds of the formula I.5 where (X)m is 3-nitro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0776] Table 348

[0777] Compounds of the formula I.5 where (X)m is 3-nitro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0778] Table 349

[0779] Compounds of the formula I.5 where (X)m is 4-nitro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0780] Table 350

[0781] Compounds of the formula I.5 where (X)m is 4-nitro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0782] Table 351

[0783] Compounds of the formula I.5 where (X)m is 4-nitro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0784] Table 352

[0785] Compounds of the formula I.5 where (X)m is 4-nitro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0786] Table 353

[0787] Compounds of the formula I.5 where (X)m is 4-nitro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0788] Table 354

[0789] Compounds of the formula I.5 where (X)m is 4-nitro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0790] Table 355

[0791] Compounds of the formula I.5 where (X)m is 5-nitro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0792] Table 356

[0793] Compounds of the formula I.5 where (X)m is 5-nitro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0794] Table 357

[0795] Compounds of the formula I.5 where (X)m is 5-nitro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0796] Table 358

[0797] Compounds of the formula I.5 where (X)m is 5-nitro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0798] Table 359

[0799] Compounds of the formula I.5 where (X)m is 5-nitro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0800] Table 360

[0801] Compounds of the formula I.5 where (X)m is 5-nitro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0802] Table 361

[0803] Compounds of the formula I.6a where m is zero, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A 18

[0804] Table 362

[0805] Compounds of the formula I.6a where m is zero, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0806] Table 363

[0807] Compounds of the formula I.6a where m is zero, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0808] Table 364

[0809] Compounds of the formula I.6a where m is zero, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0810] Table 365

[0811] Compounds of the formula I.6a where m is zero, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0812] Table 366

[0813] Compounds of the formula I.6a where m is zero, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0814] Table 367

[0815] Compounds of the formula I.6a where (X)m is 3-chloro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0816] Table 368

[0817] Compounds of the formula I.6a where (X)m is 3-chloro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0818] Table 369

[0819] Compounds of the formula I.6a where (X)m is 3-chloro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0820] Table 370

[0821] Compounds of the formula I.6a where (X)m is 3-chloro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0822] Table 371

[0823] Compounds of the formula I.6a where (X)m is 3-chloro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0824] Table 372

[0825] Compounds of the formula I.6a where (X)m is 3-chloro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0826] Table 373

[0827] Compounds of the formula I.6a where (X)m is 4-chloro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0828] Table 374

[0829] Compounds of the formula I.6a where (X)m is 4-chloro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0830] Table 375

[0831] Compounds of the formula I.6a where (X)m is 4-chloro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0832] Table 376

[0833] Compounds of the formula I.6a where (X)m is 4-chloro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0834] Table 377

[0835] Compounds of the formula I.6a where (X)m is 4-chloro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0836] Table 378

[0837] Compounds of the formula I.6a where (X)m is 4-chloro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0838] Table 379

[0839] Compounds of the formula I.6a where (X)m is 5-chloro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0840] Table 380

[0841] Compounds of the formula I.6a where (X)m is 5-chloro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0842] Table 381

[0843] Compounds of the formula I.6a where (X)m is 5-chloro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0844] Table 382

[0845] Compounds of the formula I.6a where (X)m is 5-chloro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0846] Table 383

[0847] Compounds of the formula I.6a where (X)m is 5-chloro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0848] Table 384

[0849] Compounds of the formula I6a where (X)m is 5-chloro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0850] Table 385

[0851] Compounds of the formula I.6a where (X)m is 3-bromo, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0852] Table 386

[0853] Compounds of the formula I.6a where (X)m is 3-bromo, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0854] Table 387

[0855] Compounds of the formula I.6a where (X)m is 3-bromo, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0856] Table 388

[0857] Compounds of the formula I.6a where (X)m is 3-bromo, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0858] Table 389

[0859] Compounds of the formula I.6a where (X)m is 3-bromo, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0860] Table 390

[0861] Compounds of the formula I.6a where (X)m is 3-bromo, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0862] Table 391

[0863] Compounds of the formula I.6a where (X)m is 4-bromo, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0864] Table 392

[0865] Compounds of the formula I.6a where (X)m is 4-bromo, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0866] Table 393

[0867] Compounds of the formula I.6a where (X)m is 4-bromo, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0868] Table 394

[0869] Compounds of the formula I.6a where (X)m is 4-bromo, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0870] Table 395

[0871] Compounds of the formula I.6a where (X)m is 4-bromo, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0872] Table 396

[0873] Compounds of the formula I.6a where (X)m is 4-bromo, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0874] Table 397

[0875] Compounds of the formula I.6a where (X)m is 5-bromo, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0876] Table 398

[0877] Compounds of the formula I.6a where (X)m is 5-bromo, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0878] Table 399

[0879] Compounds of the formula I.6a where (X)m is 5-bromo, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0880] Table 400

[0881] Compounds of the formula I.6a where (X)m is 5-bromo, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0882] Table 401

[0883] Compounds of the formula I.6a where (X)m is 5-bromo, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0884] Table 402

[0885] Compounds of the formula I.6a where (X)m is 5-bromo, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0886] Table 403

[0887] Compounds of the formula I.6a where (X)m is 3-nitro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0888] Table 404

[0889] Compounds of the formula I.6a where (X)m is 3-nitro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0890] Table 405

[0891] Compounds of the formula I.6a where (X)m is 3-nitro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0892] Table 406

[0893] Compounds of the formula I.6a where (X)m is 3-nitro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0894] Table 407

[0895] Compounds of the formula I.6a where (X)m is 3-nitro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0896] Table 408

[0897] Compounds of the formula I.6a where (X)m is 3-nitro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0898] Table 409

[0899] Compounds of the formula I.5a where (X)m is 4-nitro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0900] Table 410

[0901] Compounds of the formula I.6a where (X)m is 4-nitro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0902] Table 411

[0903] Compounds of the formula I.6a where (X)m is 4-nitro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0904] Table 412

[0905] Compounds of the formula I.6a where (X)m is 4-nitro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0906] Table 413

[0907] Compounds of the formula I.6a where (X)m is 4-nitro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0908] Table 414

[0909] Compounds of the formula I.6a where (X)m is 4-nitro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A

[0910] Table 415

[0911] Compounds of the formula I.6a where (X)m is 5-nitro, R2 is hydrogen and the radical R3 for each compound corresponds to one line of Table A

[0912] Table 416

[0913] Compounds of the formula I.6a where (X)m is 5-nitro, R2 is methyl and the radical R3 for each compound corresponds to one line of Table A

[0914] Table 417

[0915] Compounds of the formula I.6a where (X)m is 5-nitro, R2 is ethyl and the radical R3 for each compound corresponds to one line of Table A

[0916] Table 418

[0917] Compounds of the formula I.6a where (X)m is 5-nitro, R2 is n-propyl and the radical R3 for each compound corresponds to one line of Table A

[0918] Table 419

[0919] Compounds of the formula I.6a where (X)m is 5-nitro, R2 is isopropyl and the radical R3 for each compound corresponds to one line of Table A

[0920] Table 420

[0921] Compounds of the formula I.6a where (X)m is 5-nitro, R2 is cyano and the radical R3 for each compound corresponds to one line of Table A 1 TABLE A I 19 No. R3 Rb A-1 c-C6H11 — A-2 c-C6H10 2-Cl A-3 c-C6H10 3-Cl A-4 c-C6H10 4-Cl A-5 c-C6H10 2-Br A-6 c-C6H10 3-Br A-7 c-C6H10 4-Br A-8 c-C6H10 2-NO2 A-9 c-C6H10 3-NO2 A-10 c-C6H10 4-NO2 A-11 c-C6H10 4-NO2 A-11 c-C6H10 2-CN A-12 c-C6H10 3-CN A-13 c-C6H10 4-CN A-14 c-C6H10 2-CH3 A-15 c-C6H10 3-CH3 A-16 c-C6H10 4-CH3 A-17 c-C6H9 2,4-(Cl)2 A-18 c-C6H9 2,4-(Br)2 A-19 c-C6H9 2,4-(NO2)2 A-20 c-C6H9 2,4-(CH3)2 A-21 c-C6H10 4-CH2CH3 A-22 c-C6H10 4-CH2CH2CH3 A-23 c-C6H10 4-CH(CH3)2 A-24 c-C6H10 4-CH2CH2CH2CH3 A-25 c-C6H10 4-CH2CH(CH3)2 A-26 C6H5 — A-27 C6H4 2-Cl A-28 C5H4 3-Cl A-29 C6H4 4-Cl A-30 C6H4 2-Br A-31 C6H4 3-Br A-32 C6H4 4-Br A-33 C6H4 2-NO2 A-34 C6H4 3-NO2 A-35 C6H4 4-NO2 A-36 C6H4 2-CN A-37 C6H4 3-CN A-38 C6H4 4-CN A-39 C6H4 2-CH3 A-40 C6H4 3-CH3 A-41 C6H4 4-CH3 A-42 C6H4 4-CH2CH3 A-43 C6H4 4-CH2CH2CH3 A-44 C6H4 4-CH(CH3)2 A-45 C5H4 4-CH2CH2CH2CH3 A-46 C6H4 4-CH2CH(CH3)2 A-47 C6H4 4-C(CH3)3 A-48 C6H4 4-C6H5 A-49 C6H4 4-(2-Cl)—C6H4 A-50 C6H4 4-(3-Cl)—C6H4 A-51 C6H4 4-(4-Cl)—C6H4 A-52 C6H4 4-(2-Br)—C6H4 A-53 C6H4 4-(3-Br)—C6H4 A-54 C6H4 4-(4-Br)—C6H4 A-55 C6H4 4-(2-NO2)—C6H4 A-56 C6H4 4-(3-NO2)—C6H4 A-57 C6H4 4-(4-NO2)—C6H4 A-58 C6H4 4-(2-CN)—C6H4 A-59 C6H4 4-(3-CN)—C6H4 A-60 C6H4 4-(4-CN)—C6H4 A-61 C6H4 4-(2-CH3)—C6H4 A-62 C6H4 4-(3-CH3)—C6H4 A-63 C6H4 4-(4-CH3)—C6H4 A-64 C6H4 4-(2,4-Cl2)—C6H3 A-65 C6H4 4-(2,4-Br2)—C6H3 A-66 C6H4 4-[2,4-(NO2)2]—C6H3 A-67 C6H4 4-[2,4-(CH3)2]—C6H3

[0922] The compounds I are suitable as fungicides. They are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes. Some of them act systemically, and they can be employed in crop protection as foliar-acting and soil-acting fungicides. They are especially important for controlling a multiplicity of fungi on a series of crop plants such as wheat, rye, barley, oats, rice, maize, grass, bananas, cotton, soya, coffee, sugar cane, grapevines, fruit plants, ornamentals and vegetable plants such as cucumbers, beans, tomatoes, potatoes and cucurbits, and on the seeds of these plants.

[0923] Specifically, they are suitable for controlling the following plant diseases:

[0924] Alternaria species on vegetable and fruit,

[0925] Botrytis cinerea (gray mold) on strawberries, vegetables, ornamentals and grapevines,

[0926] Cercospora arachidicola on peanuts,

[0927] Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbits,

[0928] Erysiphe graminis (powdery mildew) on cereals,

[0929] Fusarium and Verticillium species on a variety of plants,

[0930] Helminthosporium species on cereals,

[0931] Mycosphaerella species on bananas and peanuts,

[0932] Phytophthora infestans on potatoes and tomatoes,

[0933] Plasmopara viticola on grapevines,

[0934] Podosphaera leucotricha on apples,

[0935] Pseudocercosporella herpotrichoides on wheat and barley,

[0936] Pseudoperonospora species on hops and cucumbers,

[0937] Puccinia species on cereals,

[0938] Pyricularia oryzae on rice,

[0939] Rhizoctonia species on cotton, rice and lawns,

[0940] Septoria nodorum on wheat,

[0941] Uncinula necator on grapevines,

[0942] Ustilago species on cereals and sugar cane, and

[0943] Venturia species (scab) on apples and pears.

[0944] Moreover, the compounds I are suitable for controlling harmful fungi such as Paecilomyces variotii in the protection of materials (for example wood, paper, paint dispersions, fibers and fabrics) and in the protection of stored products.

[0945] The compounds I are applied by treating the fungi, or the plants, seeds, materials to be protected against fungal infection, or the soil, with a fungicidally effective amount of the active ingredients. Application can be effected both before and after infection of the materials, plants or seeds by the fungi.

[0946] In general, the fungicidal compositions comprise from 0.1 to 95, preferably from 0.5 to 90, % by weight of active ingredient.

[0947] When used in crop protection, the application rates are from 0.01 to 2.0 kg of active ingredient per ha, depending on the nature of the desired effect.

[0948] In the treatment of seed, amounts of active ingredient of from 0.001 to 0.1 g, preferably 0.01 to 0.05 g, are generally required per kilogram of seed.

[0949] When used in the protection of materials or stored products, the application rate of active ingredient depends on the nature of the field of application and on the desired effect. Conventionally used application rates in the protection of materials are, for example, from 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active ingredient per cubic meter of material treated.

[0950] The compounds I can be converted into the customary formulations, e.g. solutions, emulsions, suspensions, dusts, powders, pastes and granules. The use form depends on the particular purpose; it is intended to ensure in each case a fine and uniform distribution of the compound according to the invention.

[0951] The formulations are prepared in a known manner, e.g. by extending the active ingredient with solvents and/or carriers, if desired using emulsifiers and dispersants, it also being possible to use other organic solvents as cosolvents if water is used as the diluent. Auxiliaries which are suitable are essentially: solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. mineral oil fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g. ethanolamine, dimethylformamide) and water; carriers such as ground natural minerals (e.g. kaolins, clays, talc, chalk) and ground synthetic minerals (e.g. highly dispersed silica, silicates); emulsifiers such as nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignin-sulfite waste liquors and methylcellulose.

[0952] Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, napthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids and their alkali metal and alkaline earth metal salts, salts of sulfated fatty alcohol glycol ether, condensates of sulfonated naphthalene and napthalene derivatives with formaldehyde, condensates of napthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctyl phenol, octyl phenol, nonyl phenol, alkyl phenyl polyglycol ethers, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin sulfite waste liquors and methyl cellulose.

[0953] Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents, e.g. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone and water.

[0954] Powders, materials for spreading and dusts can be prepared by mixing or concomitantly grinding the active substances together with a solid carrier.

[0955] Granules, e.g. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Examples of solid carriers are mineral earths, such as silica gels, silicic acids, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.

[0956] In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active ingredient. The active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

[0957] The following are examples of formulations:

[0958] I. 5 parts by weight of a compound according to the invention are mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dust which comprises 5% by weight of the active ingredient.

[0959] II. 30 parts by weight of a compound according to the invention are mixed intimately with a mixture of 92 parts by weight of pulverulent silica gel and 8 parts by weight of paraffin oil which had been sprayed onto the surface of this silica gel. This gives a formulation of the active ingredient with good adhesion properties (active ingredient content 23% by weight).

[0960] III. 10 parts by weight of a compound according to the invention are dissolved in a mixture composed of 90 parts by weight of xylene, 6 parts by weight of the adduct of 8 to 10 mol of ethylene oxide and 1 mol of oleic acid N-monoethanolamide, 2 parts by weight of calcium dodecylbenzenesulfonate and 2 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil (active ingredient content 9% by weight)

[0961] IV. 20 parts by weight of a compound according to the invention are dissolved in a mixture composed of 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 5 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil (active ingredient content 16% by weight).

[0962] V. 80 parts by weight of a compound according to the invention are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalene-alpha-sulfonate, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill (active ingredient content 80% by weight).

[0963] VI. 90 parts by weight of a compound according to the invention are mixed with 10 parts by weight of N-methyl-&agr;-pyrrolidone, which gives a solution which is suitable for use in the form of microdrops (active ingredient content 90% by weight).

[0964] VII. 20 parts by weight of a compound according to the invention are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion comprising 0.02% by weight of the active ingredient.

[0965] VIII. 20 parts by weight of a compound according to the invention are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalene-&agr;-sulfonate, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60% by weight of pulverulent silica gel, and the mixture is ground in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives a spray mixture comprising 0.1% by weight of the active ingredient.

[0966] The active ingredients can be used as such, in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend entirely on the intended purposes; they are intended to ensure in each case the finest possible distribution of the active ingredients according to the invention.

[0967] Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water.

[0968] The active ingredient concentration in the ready-to-use products can be varied within relatively wide ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to 1%.

[0969] The active ingredients may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95% by weight of active ingredient, or even to apply the active ingredient without additives.

[0970] Various types of oils, or herbicides, fungicides, other pesticides or bactericides may be added to the active ingredients, if appropriate just immediately prior to use (tank mix). These agents can be admixed with the agents according to the invention in a weight ratio of 1:10 to 10:1.

[0971] In the use form as fungicides, the compositions according to the invention can also be present together with other active ingredients, e.g. with herbicides, insecticides, growth regulators, fungicides or else with fertilizers. Mixing the compounds I or the compositions comprising them in the use form as fungicides with other fungicides frequently results in a broadened fungicidal spectrum of action.

[0972] The following list of fungicides together with which the compounds according to the invention can be used is intended to illustrate the possible combinations, but not to impose any limitation:

[0973] sulfur, dithiocarbamates and their derivatives, such as iron (III) dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediaminebisdithiocarbamate, tetramethylthiuram disulfide, ammonia complex of zinc (N,N-ethylenebisdithiocarbamate), ammonia complex of zinc (N,N′-propylenebisdithiocarbamate), zinc (N,N′-propylenebisdithiocarbamate), N,N′-polypropylenebis(thiocarbamoyl)disulfide;

[0974] nitro derivatives, such as dinitro(1-methylheptyl)phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl 3,3-dimethylacrylate, 2-sec-butyl-4,6-dinitrophenylisopropyl carbonate, diisopropyl 5-nitroisophthalate;

[0975] heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-diethyl phthalimidophosphonothioate, 5-amino-1-[bis(dimethylamino)phosphinyl]-3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithioanthraquinone, 2-thio-1,3-dithiolo[4,5-b]quinoxaline, methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate, 2-methoxycarbonylaminobenzimidazole, 2-(2-furyl)-benzimidazole, 2-(4-thiazolyl)benzimidazole, N-(1,1,2,2-tetrachloroethylthio)tetrahydrophthalimide, N-tri-chloromethylthiotetrahydrophthalimide, N-trichloromethylthiophthalimide;

[0976] N-dichlorofluoromethylthio-N′,N′-dimethyl-N-phenylsulfo-diamide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-thiocyanatomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene, 4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone, pyridine-2-thiol 1-oxide, 8-hydroxyquinoline or its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine 4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide, 2-methylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxanilide, 2,4,5-trimethylfuran-3-carboxanilide, N-cyclohexyl-2,5-dimethylfuran-3-carboxamide, N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide, 2-methylbenzanilide, 2-iodobenzanilide, N-formyl-N-morpholine-2,2,2-trichloroethyl acetal, piperazine-1,4-diylbis-1-(2,2,2-trichloroethyl)formamide, 1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane;

[0977] amines such as 2,6-dimethyl-N-tridecylmorpholine or its salts, 2,6-dimethyl-N-cyclododecylmorpholine or its salts, N-[3-(p-tert-butylphenyl)-2-methylpropyl]-cis-2,6-dimethyl-morpholine, N-[3- (p-tert-butylphenyl)-2-methylpropyl]-piperidine;

[0978] azoles such as 1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole, 1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole, N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N′-imidazolylurea, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone, 1-(4-chlorophenoxy)-3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -2-butanol, (2RS,3RS)-1-[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-yl-methyl]-1H-1,2,4-triazole, &agr;-(2-chlorophenyl)-&agr;-(4-chlorophenyl)-5-pyrimidinemethanol, 5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine, bis(p-chlorophenyl)-3-pyridinemethanol, 1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene, 1,2-bis(3-methoxycarbonyl-2-thioureido)benzene;

[0979] strobilurins such as methyl E-methoxyimino-[&agr;-(o-tolyloxy)-o-tolyl]acetate, methyl E-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxylphenyl}-3-methoxyacrylate, N-methyl-E-methoxy-imino-[&agr;-(2-phenoxyphenyl)]acetamide, N-methyl E-methoxyimino-(&agr;-(2,5-dimethylphenoxy)-o-tolyl]acetamide;

[0980] anilinopyrimidines such as N-(4,6-dimethylpyrimidin-2-yl)aniline, N-[4-methyl-6-(1-propynyl)pyrimidin-2-yl]aniline, N-[4-methyl-6-cyclopropylpyrimidin-2-yl]aniline;

[0981] phenylpyrroles such as 4-(2,2-difluoro-1,3-benzodioxol-4-yl)pyrrole-3-carbonitrile;

[0982] cinnanamides such as 3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acryloylmorpholine;

[0983] and a variety of fungicides such as dodecylguanidine acetate, 3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]glutarimide, hexachlorobenzene, methyl N-(2,6-dimethylphenyl)-N-(2-furoyl)-DL-alaninate, DL-N-(2,6-dimethylphenyl)-N-(2′-methoxyacetyl)alanine methyl ester, N-(2,6-dimethylphenyl)-N-chloroacetyl-D,L-2-aminobutyrolactone, DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)alanine methyl ester, 5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine, 3-(3,5-dichlorophenyl)5-methyl-5-methoxymethyl-1,3-oxazolidine-2,4-dione, 3-(3,5-dichlorophenyl)-1-isopropylcarbamoylhydantoin, N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide, 2-cyano-[N-(ethylaminocarbonyl)-2-methoximino]acetamide, 1-[2-(2,4-dichlorophenyl)pentyl]-1H-1,2,4-triazole, 2,4-difluoro-&agr;- (1H-1,2,4-triazolyl-1-methyl)benzhydryl alcohol, N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chloro-2-aminopyridin, 1-((bis-(4-fluorophenyl)methylsilyl)methyl)-1H-1,2,4-triazole.

SYNTHESIS EXAMPLES

[0984] The protocols shown in the synthesis examples herebelow were used for obtaining further compounds I, except that the starting compounds were changed as appropriate. The resulting compounds are listed in the tables which follow together with physical data.

Example 1 Preparation of 2-hydroxy-3-nitrobenzhydrazide

[0985] 20

[0986] 40 ml of hydrazine hydrate were added to a solution of 30 g (0.15 mol) of methyl 3-nitrosalicylate in 200 ml of anhydrous tetrahydrofuran (THF). After dilution with THF, the resulting suspension was stirrable; it was refluxed for approximately 18 hours. After cooling, the batch was poured onto ice. The aqueous solution was rendered neutral by adding NaOH solution. The crystals which precipitated were filtered off and washed with water. After drying, 27 g (90%) of the title compound were obtained.

Example 2 Preparation of 3-nitrosalicylic (1-phenylethylidene)hydrazide

[0987] 21

[0988] A solution of 1.0 g (5 mmol) of 3-nitrosalicylohydrazide in 50 ml of anhydrous ethanol were treated with 0.6 g (5 mmol) of acetophenone and with a catalytic amount of p-toluenesulfonic acid. After the mixture had been stirred for 14 hours at approximately 20 to 25° C. and the solvent had been distilled off, 1.4 g of the title compound (90% of theory) were obtained as colorless crystals of m.p.: 163-168° C. 2 TABLE I I 22 No. R1 (X)m R2 R3 M.p. [° C.] I-1 NO2 H CH3 C6H5 163-168 I-2 NO2 H H C6H5 193-199 I-3 NO2 H CH3 4-CH3—C6H4 149-154 I-4 NO2 H H 4-CH3—C6H4 160-166 I-5 NO2 H CH3 4-Cl—C6H4 194-197 I-6 NO2 H H 4-Cl—C6H4 192-196 I-7 NO2 H CH3 4-Br—C6H4 194-197 I-8 NO2 H H 4-Br—C6H4 174-178 I-9 NO2 H CH3 4-NO2—C6H4 204-208 I-10 NO2 H H 4-NO2—C6H4 240-244 I-11 NO2 H CH3 4-CN—C6H4 218-222 I-12 NO2 H H 4-CN—C6H4 220-223 I-13 NO2 H CH3 4-OCH3—C6H4 146-150 I-14 NO2 H H 4-OCH3—C6H4 167-172 I-15 NO2 H CH3 2,4-(OCH3)2—C6H4 245-248 I-16 NO2 H H 2,4-(OCH3)2—C6H4 207-210 I-17 NO2 H CH3 2,4-Cl2—C6H4 110-114 I-18 NO2 H H 2,4-Cl2—C6H4 219-223 I-19 NO2 H CH3 4-C6H5—C6H4 209-212 I-20 NO2 H H 4-C6H5—C6H4 189-195

[0989] Examples of the action against harmful fungi

[0990] The fungicidal action of the compounds of the general formula I was demonstrated by the following experiments:

[0991] The active ingredients, separately or together, were formulated as a 10% emulsion in a mixture of 70% by weight of cyclohexanone, 20% by weight of Nekanil® LN (Lutensol® AP6, wetter with emulsifier and dispersant action based on ethoxylated alkylphenols) and 10% by weight of Wettol® EM (nonionic emulsifer based on ethoxylated castor oil) and the formulations were diluted with water to give the desired concentration.

[0992] Use example—activity against Botrytis cinerea on capsicum leaves

[0993] After 4-5 leaves had developed properly, capsicum seedlings cv. “Neusiedler Ideal Elite” were sprayed to runoff point with an aqueous preparation of active ingredient made with a stock solution of 10% of active ingredient, 63% of cyclohexanone and 27% of emulsifier. Next day, the treated plants were inoculated with a spore suspension of Botrytis cinerea which contained 1.7×106 spores/ml in a 2% strength aqueous Biomite solution. The test plants were subsequently placed into a controlled-environment cabinet at 22-24° C. and high atmospheric humidity. After 5 days, it was possible to determine the extent of fungal infection on the leaves visually in %.

[0994] In this test, the disease level of the plants treated with a 250 ppm formulation of the active ingredient I-1, I-3 and I-6 was not more than 15%, while it was 90% in the case of the untreated plants.

Claims

1. A salicylohydrazide derivative of the formula I

23

in which the index and the substituents have the following meanings:

X is halogen, NO2, cyano, C1-C4-alkyl or C1-C4-alkoxy;

m is 0, 1, 2 or 3, it being possible for the substituents X to differ from each other if n is greater than 1;

R1 is NO2, NH2 or NH—CO—A;

A is hydrogen, C1-C4-alkyl, C1-C4-alkoxy, NH2, NHCH3 or N(CH3)2;

R2 is hydrogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-alkylthio;

it being possible for the hydrocarbon radicals to be unsubstituted or to be partially or fully halogenated or to have 1 to 3 groups Ra

Ra is halogen, cyano, nitro, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino,

di-C1-C6-alkylamino, C2-C6-alkenyl, C3-C6-alkenyloxy, C3-C6-alkynyloxy or C1-C4-alkylenedioxy which can be halogenated,

R3 is phenyl, naphthyl, C3-C10-cycloalkyl, 5-membered or 6-membered hetaryl or 5-membered or 6-membered heterocyclyl containing one to three n atoms and/or one O or s atom or one or two O and/or s atoms, the ring systems being unsubstituted or substituted by one to three radicals Rb:

Rb is cyano, nitro, amino, aminocarbonyl, aminothiocarbonyl, halogen, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkyloxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, phenyl, phenoxy, benzyl, benzyloxy, 5- or 6-membered heterocyclyl, 5- or 6-membered hetaryl, 5- or 6-membered hetaryloxy, C(═NOR&agr;)—OR&bgr; or OC(R&agr;)2—C(R&bgr;)═NOR&bgr;,

the cyclic radicals, in turn, being unsubstituted or substituted by one to three radicals Rc:

Rc is cyano, nitro, halogen, hydroxyl, amino, aminocarbonyl, aminothiocarbonyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, phenyl, phenoxy, phenylthio, benzyl, benzyloxy, 5- or 6-membered heterocyclyl, 5- or 6-membered hetaryl, 5- or 6-membered hetaryloxy or C(═NOR&agr;)—OR&bgr;,

R&agr;, R&bgr; are hydrogen or C1-C6-alkyl.

2. A compound of the formula I as claimed in claim 1 where R1 is NH—CO—A.

3. A compound of the formula I as claimed in claim 1 where m is zero.

4. A compound of the formula I as claimed in claim 1 where m is 1 and X is in the 4-position.

5. A compound of the formula I as claimed in claim 1 where

A is hydrogen, C1-C4-alkoxy, NHCH3 or N(CH3)2:

R2 is CN or C1-C6-alkyl;

R3 is phenyl or 5-membered or 6-membered hetaryl, the ring systems being unsubstituted or substituted by one to three radicals Rb.

6. A process for the preparation of compounds of the formula I as claimed in claim 1 by reacting hydrazides of the formula II

24

with carbonyl compounds of the formula III

25

to give compounds of the formula I where R1 is NO2,

26

and, to prepare compounds I where R1 is NH2 or NH—CO—A, hydrogenating IA to give aminophenol compounds of the formula IB,

27

and, to prepare compounds I where R1 is NH—CO—H, formylation of IB to give compounds of the formula I.1

28

or, to prepare compounds I where R1 is NH—CO—NH2, reacting Is with alkali metal isocyanates or alkaline earth metal isocyanates to give compounds of the formula I.2,

29

or, to prepare compounds I where R1 is NH—CO—NHCH3, reacting IB with methyl isocyanate to give compounds of the formula I.3,

30

or, to prepare compounds I where R1 is NH—CO—N(CH3)2, reacting IB with phosgene and dimethylamine to give compounds of the formula I.4,

31

or, to prepare compounds I in which R1 is NH—CO—OCH3, reacting In with carbon monoxide and methanol with transition-metal catalysis to give compounds of the formula I.5

32

7. The use of the compounds of the formulae IA and IB as intermediates.

8. A composition which is suitable for controlling phytopathogenic harmful fungi, comprising a solid or liquid carrier and a compound of the formula I as claimed in claim 1.

9. A method of controlling phytopathogenic harmful fungi, which comprises treating the fungi, or the materials, plants, the soil or seed to be protected from fungal attack, with an effective amount of a compound of the formula I as claimed in claim 1.